Pienza Villas - Best Villa Pienza 2026

A historic square with a prominent tower and statues.

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Our top choices for Pienza villas

A two-story building with balconies, outdoor seating, and potted plants.

1. Artisti del Cavallo Tourism

Foiano della Chiana

Heiner

includes taxes & fees

29 Oct - 30 Oct

A stone building with multiple rooms, surrounded by lush greenery and trees.

2. WPRELAIS BORGO VIGNALUNGA

Toscana

Jeremy F.

A courtyard with a pathway leading to a circular garden area, surrounded by trees and a building with a tiled roof.

3. Elegant ground floor villa of 93 m2 consisting of a large living room with sofas and fireplace, kitchen complete with dishwasher, microwave oven, electric oven, coffee machine, kettle, fridge and freezer.Indoor and outdoor dining area, a double bedroom w

Trequanda

includes taxes & fees

11 Nov - 12 Nov

A stone building with a tiled roof, a small porch, and a pathway leading to it.

4. Villa "Podere Spagliarda" with Private Pool, Terrace & Wi-Fi

San Quirico d'Orcia

A stone house with a sloped roof, a wooden porch, and a garden with various plants and flowers.

5. Il Poggio dell'Eremita

Sinalunga

Paul Q.

includes taxes & fees

29 Oct - 30 Oct

A tree, a lamp post, and a clear blue pool with a view of distant mountains.

6. Villa 'Tiberini - Casale Il Pecino' with panoramic Valdichiana view, private pool & Wi-Fi

Torrita di Siena

"Our first trip to Tuscany was made extra special by our accommodations. From the moment we arrived, our hosts Nunzia and Luca were so attentive to all our needs. They made sure we had great recommendations. We even spent a few hours at their house doing wine tasting and a tour of their operation. Make sure you get to try Day 1 wine…was my favorite!! Would highly recommend this location as a great landing spot in Tuscany. Located so close to many great little villages."

Nate D.

includes taxes & fees

11 Nov - 12 Nov

A patio with a table and chairs, a large umbrella, and a vase of flowers.

7. Villa Cielo- Cignella Resort Tuscany Accommodation

Trequanda

includes taxes & fees

3 Nov - 4 Nov

A patio table with a patterned tablecloth, an umbrella, and metal chairs.

8. Villa Falco-Cignella Resort Apartments in Tuscany

Trequanda

includes taxes & fees

11 Nov - 12 Nov

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Top Pienza Hotel Reviews

Hotel Corsignano

10/10 Excellent

"Excellent hotel. We had a superior room which was large and had a fabulous bathroom. The views over the valley were beautiful. The staff were really nice. We enjoyed chilling on the terrace solarium when we weren't exploring the lovely old town."

Agriturismo Poggio Tobruk

10/10 Excellent

"Did you ever want to say that you stayed in one of the Pope's guest houses? The Agriturismo Poggio Tobruk may be a place for you, and that is only a starter. The Poggio is a working farm (wheat, clover, olives) and it is managed by Marco, a Sardinaian, and his brother. Marco works the villa as well as running the farm with his brother. One of our group worked a wheat farm in Colorado, so a lot of time was spent looking at equipment and discussing crops. We picniked in the olive grove and basked on the lawn, both with marvelous views of the countryside and Pienza on its own hill just a few kilometers away. We bought products from the farm, and of course the friendly Marco gave us more products to take along. Poggio Tobruk is a great place to visit, and not just because the Pope once hosted guests there!"

Castello di Velona Resort Thermal SPA & Winery

10/10 Excellent

"Stayed at the hotel for our honeymoon and it was an incredible experience. The view is simply breathtaking and the castle is extremely charming. Food (breakfast and diner) and wine at the restaurants are high quality, inspired and locally sourced, though expensive. Their Brunello is VERY good. The thermal spa experience is unique in the region and is awsome, especially during the fall season when it is cooler outside. The room was super clean and the staff was very helpful throughout the entire week, and we felt welcomed at any time of day. 15 min by car from Montalcino, strongly recommend to rent a car since it is slightly remote. Overall 9.5/10, strongly recommend for a special occasion."

Find out more about Pienza

Pienza Villas information

Number of reviews	121
Accommodation	1372 Villas
Lowest Price	€84
Highest Price	€5,928

Frequently asked questions

How much do villas in Pienza cost?

Rates for villas in Pienza range between €84 and €5,928 per night. Whatever your budget, you're sure to find a place that fits the bill with Expedia. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.

How many villas are there in Pienza?

Pack your suitcase and pick from 1372 villas in Pienza. For a family escape, a getaway with pals or anything in between, Expedia will help you find the right place in just a click or two.

Why book your villa in Pienza with Expedia?

With Expedia, it's easy to find your dream villa in Pienza. Holidaying with the kids? Use our helpful filters to search for stays with amenities like WiFi and a pool. If you have a certain budget, select how much you'd like to spend and your preferred star rating. We'll help you find the right stay in tune with your taste and style.

How can I find cheap villas in Pienza?

An excellent way to track down cheap villas in Pienza is with Expedia's user-friendly filter tool. Narrow your search results by budget, star rating and amenities to find unbeatable rates in just a click or two.

What is there to do near my villa in Pienza?

Whatever you're interested in, Pienza has plenty to keep you going. Artemisia Gallery, Pienza Cathedral and Palazzo Comunale are on many visitors' sightseeing itineraries. Don't forget about Palazzo Piccolomini, Historic Centre of Pienza and Piazza Pio II either. With Expedia's hotel deals in Pienza, you can discover more neat attractions like these with the money you save.

Room 1

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Pienza villas

1. Artisti del Cavallo Tourism

2. WPRELAIS BORGO VIGNALUNGA

3. Elegant ground floor villa of 93 m2 consisting of a large living room with sofas and fireplace, kitchen complete with dishwasher, microwave oven, electric oven, coffee machine, kettle, fridge and freezer.Indoor and outdoor dining area, a double bedroom w

4. Villa "Podere Spagliarda" with Private Pool, Terrace & Wi-Fi

5. Il Poggio dell'Eremita

6. Villa 'Tiberini - Casale Il Pecino' with panoramic Valdichiana view, private pool & Wi-Fi

7. Villa Cielo- Cignella Resort Tuscany Accommodation

8. Villa Falco-Cignella Resort Apartments in Tuscany

9. '...a delicious farmhouse in the countryside where only the wind blows...'

10. VILLA BRUNELLO - Luxury Country Retreat 10 minutes to Montalcino

11. Red Heart - Relax with Your Loved Ones in Tuscany

12. Apartment In A Hotel "Villa Pesca" with Shared Pool, Private Balcony & Wi-Fi

13. Villa Aquila-Cignella Resort Acommodation Tuscany

14. Elegant ground floor villa of 93 m2 consisting of a large living room with sofas and fireplace, kitchen complete with dishwasher, microwave oven, electric oven, coffee machine, kettle, fridge and freezer.Indoor and outdoor dining area, a double bedroom w

15. Godiluva, Weinvilla

16. Elegant and spacious two-storey villa of 142 m2 composed on the ground floor of a large living room, kitchen complete with dishwasher, microwave oven, electric oven, coffee machine, kettle, fridge and freezer.On the first floor we find a double bedroom w

17. VILLA CHIGI - Seven Bedroom Villa, Sleeps 14

18. Apartment In A Hotel "Villa Cielo" with Shared Pool, Private Terrace & Wi-Fi

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Top Pienza Hotel Reviews

Hotel Corsignano

Monastero di Cortona Hotel & Spa

Nuovo Etruria Resort

Agriturismo Poggio Tobruk

Fonteverde Thermal Spa Resort Tuscany

Hotel San Gregorio

Castello di Velona Resort Thermal SPA & Winery

Castiglion del Bosco, A Rosewood Hotel

Hotel Villa Ricci

Find out more about Pienza

Pienza Villas information

Frequently asked questions

Search Villas in Pienza

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Pienza villas

1. Artisti del Cavallo Tourism

2. WPRELAIS BORGO VIGNALUNGA

3. Elegant ground floor villa of 93 m2 consisting of a large living room with sofas and fireplace, kitchen complete with dishwasher, microwave oven, electric oven, coffee machine, kettle, fridge and freezer.Indoor and outdoor dining area, a double bedroom w

4. Villa "Podere Spagliarda" with Private Pool, Terrace & Wi-Fi

5. Il Poggio dell'Eremita

6. Villa 'Tiberini - Casale Il Pecino' with panoramic Valdichiana view, private pool & Wi-Fi

7. Villa Cielo- Cignella Resort Tuscany Accommodation

8. Villa Falco-Cignella Resort Apartments in Tuscany

9. '...a delicious farmhouse in the countryside where only the wind blows...'

10. VILLA BRUNELLO - Luxury Country Retreat 10 minutes to Montalcino

11. Red Heart - Relax with Your Loved Ones in Tuscany

12. Apartment In A Hotel "Villa Pesca" with Shared Pool, Private Balcony & Wi-Fi

13. Villa Aquila-Cignella Resort Acommodation Tuscany

14. Elegant ground floor villa of 93 m2 consisting of a large living room with sofas and fireplace, kitchen complete with dishwasher, microwave oven, electric oven, coffee machine, kettle, fridge and freezer.Indoor and outdoor dining area, a double bedroom w

15. Godiluva, Weinvilla

16. Elegant and spacious two-storey villa of 142 m2 composed on the ground floor of a large living room, kitchen complete with dishwasher, microwave oven, electric oven, coffee machine, kettle, fridge and freezer.On the first floor we find a double bedroom w

17. VILLA CHIGI - Seven Bedroom Villa, Sleeps 14

18. Apartment In A Hotel "Villa Cielo" with Shared Pool, Private Terrace & Wi-Fi

Find holiday rentals that suit your style

Top Pienza Hotel Reviews

Hotel Corsignano

Find out more about Pienza

Pienza Villas information

Frequently asked questions